There's this belief that everybody needs to be a founder. I think in some ways, our industry would be much better off if there were fewer founders. There's an entire category of smart, creative, hardworking, talented, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never going to go anywhere that would be so much better off
finding a team that needs their skill set and working on a problem that has a mathematical formula that's going to win on any metric. Whatever metric you care about, you want like the acclaim of your peers, you want financial reward, you want outside impact on culture, whatever. Whatever the thing is, it gets you out of bed every morning, you can achieve that in collaboration with others. You don't have to be the person that raises the sea ground.
Today, my guest is Tom Conrad. Tom was an engineer at Apple, CTO of Pandora, which he helped take from zero to 80 million users. He's also VP of product at Snap, where he's the right-hand man to Evan Spiegel for two years. He's been on the board of Sonos for over seven years. He's also part of two infamous product failures, Quibi, where he was chief product officer, which raised over $2 billion and died less than a year after launch.
He was also a senior engineering leader at pets.com, which famously went from nothing to a public company to completely out of business in 19 months. Today, Tom is the CEO of Zero Longevity Science, which is on a mission to extend the lifespan and the health span of the human race. In our conversation, we dig into what Tom's learned from these famous product failures, also what he's learned from the many product successes.
Tom also shares what he's learned about how to pick where to go work and what to avoid, how important understanding the math formula of the business model is, also lessons on burnout and health and leadership, and contrarian corner. With that, I bring you Tom Conrad, after a short word from our sponsors.
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Tom, thank you so much for being here. Welcome to the podcast. Thank you. It's so fun to get to get part of this. I thought it'd be fun to start with a story about your time at Apple and you building this now very ubiquitous feature of dragging and dropping something into a folder, which is how you tweet about or talk about it and talk. And the fact that it's still around, you just share that story and maybe a lesson from that experience that you've taken away. Sure. So.
Let's see, I was 15 years old when the Macintosh came out.
I remember really clearly my entire teenagers, all I wanted to do was to move from Columbus, Ohio to Cupertino and work for Apple. And my heroes were, that team of people that had written their signatures on the inside of the Macintosh and you cracked open the first Macintosh case, you would find the signatures of the 20 people or so who worked on the Mac. And that was my only ambition, truly.
And this was a period where no one wanted to work for Apple. I mean, that wasn't a thing. And it seems like maybe a little obvious today, but it wasn't an obvious ambition at all. So anyway, I went to college. So I wanted to do study computer engineering at University of Michigan. And as we talk about my career, it's just over and over and over. I'm going to say,
an incredibly lefty thing happened and the first incredibly lefty thing that happened for me in my career probably was that University of Michigan like happened to be a place that Apple recruited from. I didn't know that when I chose the school, but it made it reasonably easy to connect to a hiring app manager at Apple and I wrote an actual letter and put it in actual envelope and put it in the mail and got an internship and drove out and my dad's Pontiac from the Midwest to California. It's been a summer interning
And my, my last day of the internship, I was thinking about really what I wanted to do when I came back, hopefully came back to Apple after I graduated. I had worked on a product that became like shipped. It was called the quick draw GX is early kind of second generation rendering system for the Mac. I've been in that team's intern for the summer. But what I really wanted to do is I wanted to work on the finder, like,
This is the only thing in the whole world I really wanted to do. So I went and found Ron Lickd, who is the manager of the Finder team and said, I graduate in 10 months. I'd love to be a part of your team. And I think he was kind of like, well, why are you coming and talking to me now? You're literally going back to Michigan tomorrow. So I go back to Michigan in May, the phone rings. And Ron says,
The college recruiting department just told me that I have a college hiring wreck. And if I don't use it by tomorrow, I lose it. So he's like, I can't even interview you. You can't meet the team, but you're basically a freebie for me. So do you want this job? So just insanely lucky moment got this job. So yeah, I get to Apple in the summer of 1992.
And I have a laundry list of things that I would like to do to make the finder more usable. And I remember sitting in Ron's office and saying, you know, the grocery store, when you're carrying bags of groceries out, the door is automatically open for you.
I think that the Finder should do the same thing when you're dragging an icon around and you want to put it in a folder, you should be able to hover maybe over the folder icons and drill down into the file system to get to where you're going. And then when you drop the file, all of the folders that opened up between you and your source and your destination would close for you.
Ronda, that was a fine idea. And so that was the way Apple worked in those days. I just went off and started, you know, coding that up. And I got to the point in the late one night, two in the morning in my Apple, no one else was there, where I needed some kind of animation to indicate that the folder was about to open.
And I'm certainly not an animator, and I certainly wasn't going to do anything awful in the middle of the night. So I just wrote some code that blinked the folder, like, selected, unselected, unselected five times. And I thought, oh, I'll get, you know, one of the really talented visual designers to do something much more interesting.
Long story short, Apple finally shipped that feature like four years later. We sat in the source code repository forever while we did other things. And when it shipped four years later, it blinked five times. Roll the clock forward six or seven years. macOS 10 comes out. Entirely new finder written from, rewritten from scratch. No spring loaded folders anywhere to be seen.
People complained about it. It got re-implemented. So all of the code, brand new, folder blinks five times when you're ever over it. Rolled the clock forward another decade. iOS comes along and they added folders. And when you drag an icon around, it blinks a few times. I'm not sure the point of this story is other than maybe it's something about
I think we all do this as designers and product people. We take these shortcuts that we think that we'll go back later and clean up. And sometimes, I mean, it's literally been 30 years, you know, that little design detail, like lingers, you know, three implementations later. And now it's just a part of the way that these Apple products work pretty bizarre.
As you were talking, I'm on a Mac right now recording this and I just did it just to make sure it's still there and it is indeed still there. I think it blinks three times and then just opens up for you. Yeah. Full engineers got royalties on features they build that continue to live on in a product. Okay, I'll tell you like just one other little thing to like.
centered you in time about what the Finder was like in 1992. We didn't get royalties, but our names were in the about box. Like you would go to about the Finder and like the seven of us, there were seven engineers at Apple that worked on the Finder. Like our names would scroll by, you know, the Finder copyright in 1992. You know, yeah, yeah, yeah. One name after another. Totally different era.
It feels like you got kind of what you wanted with the name scribbled on the motherboard. For sure. I've gotten a lot of the things I wanted as a kid.
So kind of along the same lines, I want to talk a bit about picking where to go work. Clearly you had a sense you wanted to go work at Apple. Over your career, you've landed at a lot of really successful places. You also landed at a lot of very famous failures that we're going to talk about. What advice would you give people for helping them pick where to go work based on your experience? When I was a kid, my additional work at Apple is like entirely about the product. And so probably that version of me would say,
Find a product that you're passionate about and go spend your time and energy on that thing. Pretty quickly, you learn that an awful lot of your development and day-to-day satisfaction really comes from the people that you get to collaborate with. Can you learn from them? Do you like them? Do they challenge you in the right ways? Do they give you latitude in the right ways? It's so much about not just what, but who?
And so for a very long time, my advice would have been entirely in the category of like, find something that you love with people that you think are amazing, and the rest will kind of take care of itself. And interestingly, like, I have been lucky enough to have some things that were successful, you know, on the metrics get talked about the most big audiences, big financial return, et cetera, et cetera. And I've also worked on some things that were like,
you know, really notable disasters. My sort of, when I look back on my career and like think about the things that I've done, my professional satisfaction is not well correlated with those sort of external metrics and very, very coordinated with, you know, I love the thing we were building and I love the people I was working with.
Following the threat of the people, I think one of the hardest things is really knowing what the people are like until you join. I think as a chief product officer joining or VP of product, you have a lot of time that you spend with the team. Most people don't. They have like an interview and then they're like, all right, I got to make a decision. Do you have any advice for how to help people get a sense of if the people are the kind of people they want to work with? I think people are really, really good at this.
I mean, every single time I've taken a job where it turned out that I was working with people who had a different set of values or working styles than I had, I knew. And you tell yourself that,
At least in my case, I tell myself the story about why the thing, I suspect, you know, might be the case, you know, isn't the case, but, you know, I mean, you do this in your personal life all the time, right? You meet people out at dinner, so you get, you know, seated next to them at some industry event or something, and sometimes you come home and say to your partner, oh my gosh, the person next to me was just the worst.
And then sometimes you're like, I think I made like a permanent lifelong connection with this total stranger who just happened to sit next to me. Like, you know, it's like a very simple piece of advice that I think people don't fully appreciate is just like trust your instinct, trust your gut. Yeah. Pay attention to what comes up when you're around people at a certain company.
Okay, so you brought up this phrase of notable disasters, and I want to talk about that. You worked at two of the most famous notable disasters of product companies, pets.com and Quibi. I think it's really rare. Someone sees.
the inside of so much hype and then such a fall at a company. And so I just want to spend some time in these two areas. And maybe the way to set it up is just what's a lesson you took away from each of these two experiences that you've taken with you to future work and maybe twice you share with people. Probably the biggest lesson. It's not really about like the specifics of the business. The biggest lesson really is these things make you better.
In some instances, actually, I think in both instances, they became kind of dominoes that opened doors for me in my own ambition and my own sort of professional life that maybe just wouldn't have opened at all if I hadn't gone to those companies and learned those things and had those experiences. And frankly, even in the case of pets.com, even the high profile nature of it, I could have worked it.
you know, one of a thousand e-commerce websites in 1999. And when it went on to some subsequent job interview or something and talked about my experience, we were like, I would never heard of the thing that you worked on. But everybody certainly heard about pets.com. It's a pretty funny example too of how some struggles are like timeless, you know, that was 20, 23, 24 years ago now. And
While as a leadership team, we made, I'm sure, all kinds of mistakes. One of the things that happened was that there were three kind of overfunded pet e-commerce sites. And we all raised in excess of $50 million.
which is a tremendous amount of money now. It was a tremendous amount of money then. And we all thought it was a zero sum game and that we, as one player started to spend on promotion or to spend irrationally on national broadcast television advertising, we all did.
And it became this kind of unwinnable arms race. So there was a fundamental lesson about having an excess of investment can be its own arbitrage or lead you to make decisions that maybe it would be unwise. And then, of course, it's just like,
Timing is really important. Chewy is an online pet store for $9 billion today. They were a private company and bought by PetSmartt and then spun back out, but when they were bought by PetSmartt, they were required for $3 billion.
biggest e-commerce acquisition of all time. I think it's probably unfair to compare Chewie who executed exceptionally well over a decade, grew their business brick by brick, and turned it into something really remarkable to Pest.com, which was in a very, very different moment in time and tried to go to market in a really different way.
The critique that is often leveled at Petz.com, or at least at the time, was like, this is just a stupid business. They're shipping dogs through around. You could never make that work. And that's just wrong. You absolutely can make it work. Probably can't make it work when 80% of the country on the internet is still on dial up. It was really, really early. I saw a stat, I think you shared somewhere that you took Petz.com from nothing to a public company to completely out of business in 19 months.
Yeah. Yeah. The thing that's about right. You know, the, the other thing that's forgotten in the tale is that we
We actually didn't go bankrupt. We shut the company down and returned the remaining balance to the investors with no public company had ever done before. And the leadership team just reached the conclusion that given the way market conditions had evolved, there was just no way we were gonna be able to get our capital into the company. And it was a company that required additional investment to get to profitability. And so it was better to sort of wind down early
Take the money that we had in the bank and get it back to investors, then to just spend every last penny on what was a fruitless attempt to salvage it. Let's talk about Quibi. What went wrong there? Do you think there was a path to Quibi having worked out any big lessons they took away from that experience that you bring with you?
The kind of miraculous thing about Quibi for me was it really lit my enthusiasm for the industry for doing this work. I had left in
I think it was December of 2018, and I thought that maybe I was just done making software. I had done it for a really long time, and then for like 25 years or something, and I had changed a lot, the industry had changed a lot, and I thought maybe I just didn't have the same passion for it that I had, you know, a decade before. It also seemed like maybe it would be fun to have like another chapter of my life
that was just completely different. And I had a whole list of things that I thought I might want to do. I mean, they were really, they're kind of ridiculous. It's like, maybe I want to be a pastry chef. Maybe I want to be a landscape photographer. Maybe I want to, you know, learn to make bad music to put up on SoundCloud or something. And the really, the only thing they had in common were they were all things that I knew nothing about.
People would be like, oh, you think you might want to be a pastry chef? Do you like to bake? And I'd be like, no, I don't know anything about baking. You know, oh, my landscape photography. Do you take photos? No, I don't make photos. But I was kind of committed to the bit, actually, to the point where when TechCrunch interviewed me about my departure from Snapchat, I was like, you know, I'm out. I'm going to do something else entirely. That story is very much out there. But a few months after my last day at Snap, I got a call from
Meg Whitman and Jeffrey Katzenberg, who were starting up, who's from new TV at the time. And you know, the pitch was we're gonna try to take the best of mobile and Silicon Valley and consumer tech and sort of weld it to the best of sort of Hollywood style content production to build something like completely bespoke and purpose-made for consumption on the phone.
They were looking for both technology leadership and product leadership and wanted to know if I was interested in one or both. And I took the meeting, even though I wasn't only taking these kinds of calls from anybody, it just seemed like who's gonna pass up the opportunity to have one trip with the two of them. So I listened to the pitch and politely declined and told them that I was gonna be pastry chef or something. And we kept doing that every couple of months for like seven months.
We go to lunch, they would give me an update on the progress they're making, and I would decline the invitation to get involved somehow. And then late in that year, I
I went to lunch one more time, and Meg explained that they brought on someone to lead technology, and they brought another person to lead product, and both of them, for really truly for reasons that are completely disconnected from Clibi itself, both of them had left after about six weeks. And Meg's like, we've raised all this money.
And we've told the world that we're shipping this product in about a year. We got an awful lot to do, and I really could use some help. And I would consider it a personal favor if you would become, it's been just a couple days a week helping. She's like, I'll continue to look for someone who actually wants the job, but it would really be great if you could help me get this off the ground.
And my wife is a freelance writer, marketing strategist, and loves her life as a freelance contributor. And she's like, you should do this. Like why not? It's two days a week. It's just a few months. What's the worst thing that could happen? Like maybe you'll like it. And I'm like, no, no, the worst. Here's the thing that will happen. Like I won't do it two days a week. It will like immediately be three days, then four days, then five days, then six days. Like I just know myself. And she's like, no, she's like,
You know, just on Wednesday night at six o'clock, close your Quibi laptop and be like, all they're paying before is for Tuesday and Wednesday, and then open it back up on Tuesday morning. Like, that's all you've got to do. Well,
you know, she's right about most things that she's wrong about this. I fell deeply into it right away. And it was just so fun to get to build a team from scratch and to design and build a product from scratch and to take advantage of all of the sort of modern software architecture stuff that had come into being over the course of the 15 years since we had started Pandora. And, you know, I'm
I'm embarrassed about some of what happened with Quibi for sure, but I'm super grateful for the experience because I just really fell in love with the industry again and was reminded of just how rewarding it can be to build something and to try to put it out there even if you stumble pretty mightily along the way.
Is there something that you took away from that experience that taught you what to try to avoid, what to try to pull towards? I think I sort of misunderstood or misjudged companies sometimes by thinking about them, like really focused on the product execution, you know, kind of.
If you find an interesting problem that people, you know, people care about and you solve that problem in a really beautiful, elegant, delightful way, that's 10 times better than anything else that they can get in that same space, they'll tell their friends and like all the resources will sort of take care of itself. And so that was always my ambition, find a thing that I could about building, do a great job building it really delightful way.
go really deep on listening to people and their feedback and iterate your way to success and for breaking through that membrane that we all strive to get across the kind of really great word of mouth. But I think the thing I've come to better appreciate is that
Companies are also kind of like a, they're kind of a math problem that describes how you take, you know, investment and pour them into the equation and out the other side comes returns on some time horizon. And yes.
There are variables in that equation that are influenced by the product that you build and all of the little details and decisions that you make about making that product great. But if the equation is fundamentally broken or a big swing in and of itself, no amount of iteration and execution can kind of get you out of the failed outputs of the broken equation. And I think, you know,
Quibi made a bet that you could build an entirely bespoke content library that was sufficiently scaled to get people to subscribe and retain for a couple billion dollars. It was a huge amount of money, but we made 70 shows.
in 18 months, which is more content than all of the major broadcast networks combined made in a single year. So this is a pretty major accomplishment. And we made a bet that we would augment those sort of episodic and serialized for Hollywood-style shows with a bunch of daily content that we produce
at the level of network television, nightly news, and so forth, that would be an alternative to some of the daily content that you might otherwise get on YouTube. And that was gonna be about a third of the content spend. One super interesting thing that no one talks about is that all of that content was designed to be made like day of or day before it aired. So there was no back catalog of it.
And it was all designed to be shot in these professional studios that we built out. And it was really expensive. Like I said, it was like a third of the investment we're gonna make in content, maybe half, almost half the investment we're gonna make in content. And we launched two weeks into COVID and we couldn't make any of that content except literally in the garages of the host's homes.
And so we had this thing that was supposed to seem like really set apart from YouTube that literally now was being made exactly like YouTube content, which is sort of like self-produced at home with, you know, very little sort of the support infrastructure of Hollywood. Now, you can argue, I mean, I think the content on YouTube is really, really exceptional in this category. And maybe we were never going to do better than that. But I think it was really fundamentally Burglith Quiddie.
was that the actual foundational equation of can you make enough premium content that's totally bespoke and made for the service and takes advantage of the nature of the phone. It is that enough content to get people to sign up and retain.
And can you do that for a couple of billion dollars? And I think the answer is no. The library has to be much, much bigger. And you have to have like any company, you have to have sufficient time and energy to iterate on the content format itself, because we were really, our roadmap really wanted to innovate on the content format.
And so I think part of what happened is pretty quickly it became clear that the math was just wrong. It wasn't going to take two billion. It was going to take six or eight or 10 billion and the risk reward profile of betting 10 billion on the format was just more than anyone can study.
Wow, I really like this metaphor and this mental model of the math formula of the entire business and thinking of it that way. I knew COVID changed the way people consumed content and that hurt because I think it was meant to be on the go. Sitting at home, we could watch anything you want. But also the fact that the content couldn't be made as well as you were hoping to make. Yeah, for sure. Yeah. There's a CPO.
One of the biggest challenges is pushing back, trying to convince the founders of their mistakes, of convincing, of doing what they want and just powering through it and dealing with it sometimes. I guess is there anything you think you could have done looking back or is the math formula set up for failure from the beginning? And it's probably just not going to work out almost no matter what you did. One of the bets was that
We weren't going to just use the apparatus of Hollywood to, like, make the content. In part, we were going to use the apparatus of Hollywood to market the content. So, you know, Jeffrey had recruited this incredible Rolodex of the world's, literally, the world's most famous celebrities to make shows for Quibi. We kind of had, like, everyone either made something for lunch or was going to make something.
And part of what they're going to do is turn up in culture and talk about their shows. We've heard a lot in the last six months about how hard it is to market movies because the stars can't go out and talk about the movies during the strike. There was this theory that you could apply the marketing technique of Hollywood to get
20, 30 million people into the theater on like opening weekend for Quibi. And that was always like a very, very audacious take, I thought. Like, you know, Hoover has all the money in the world to experiment with paid user acquisition. And they're not consistently a top 10 most downloaded app in the App Store.
But the theory of Quibi, like the math of Quibi, like did require us to like from day one, land in the top 10 and stay there forever. Like the model would have worked if we could do that. And to the Hollywood marketing apparatus, the numbers that it takes to get there felt kind of small. You know, if you can get 20 million people in to see Shrek on opening night, new IP, like surely you can get them to take their front out of their pocket and download this thing and start a free trial.
Now, those of us who spend our life in Silicon Valley making software and, you know,
really, really tried to get people to show up and, you know, download new IP in large numbers, know just how hard that is. So maybe if I critique my own contribution to the math equation, maybe I should have beat the drum a little harder about just how unlikely it was that we were going to land the kind of distribution in month one that the model sort of required. I
I've had it go back and do it again. I think I would spend maybe more time investing and in illuminating that aspect of the digital universe. What is such a good takeaway of just showing the leaders, here's the data, here's the assumptions that we're all betting on and do you believe this can happen? And they probably would have said, yes, this will happen. I'm so confident. What made it hard was
It wasn't structurally impossible. If you had to be bigger than any app that had ever been made, then you could probably make the case it's impossible. But since you only sort of had the land in the top 10, you couldn't quite say it was impossible. You could just say it was highly improbable. And maybe one of my mistakes was, I guess, I imagined that we would launch
And when the likely thing happened that we got millions of people to download the app, which we did, and then that when we inevitably struggled to retain those users and
high percentages. I mean, retained. It's sort of what I think of as like a good industry starting point, but, but we weren't setting any records on retention. I just imagine that what would happen next is like the thing that happens in all young companies, you would iterate. You would like grind on the funnel until a year later, two years later, six months later, whatever it is, you, you figured the formula out to get people in and get them to stay and get them to retain. And
But I didn't appreciate with like just how quickly you go back to the foundational math. And then the math really says like, you just can't, you can't spend two years iterating your way on, you know, optimizing the funnels like you would in a startup that had a different cost structure, like in a world where you have to spend, you know, a billion dollars a year making content, you just can't afford to not be a hit.
I think it's also important to just remind us it's okay for these things to happen. People take a bet. As you said, we're going to try this thing. Here's our bet. Here's our experiment. We're betting on this sort of format and this business. We're going to raise money from investors that know they might lose all their money and it sometimes doesn't work out. It's part of the game. It's certainly painful to take money from investors even if they know what they're doing and to not get them a return. I feel a real responsibility to investors to do better than we did.
at Quibi. But yeah, I mean, there is a risk-reward thing that goes along with these investments. And part of the reason I get all the riches on the upside is that they're going to bet on some Quibi's line the way to. So as you were talking, you said that it was called new TV and that sparked a memory and I searched my email. And I actually got an email from a recruiter in 2018.
We just kicked off a very special executive opportunity, the CPO at New TV, New Venture in Los Angeles with Jeffrey Katzenberg and Meg Whitman, raising a billion dollars working with top talent. Are you interested in exploring this opportunity? Lenny, Lenny, Lenny, your story could have been so much different. This could have been Thomas Podcasts. Lenny, tell me about what happened. It could be. I would take that free.
I don't know. There's pros and cons. They even sent this whole PDF. A TV in your pocket. New TV. Amazing. All right. I'm going to read through this and see what they pitched back in the day.
Okay, let's move on to things that worked out really well, what's called notable successes, other products you worked on that worked out great. So I'll list a few of them. And maybe what might be helpful is just, we'll just go through each one and share what you took away from that experience lesson you learned from working on those products. And the ones that come to mind for me are Snap, Pandora,
Apple, if we want to go there. Also, you built, I don't know exactly what you did there, but you worked on, you don't know Jack this game that I loved. I think if you're an elder millennial, you're just going to like, oh my God, I love that game. I just, I don't even remember it exactly, but I just remember the visceral feeling of playing that game and it was so much fun. So that's cool. I didn't know that you worked on that. And then there's also Sonos, which are on the board. So whatever order you think might be most interesting, just going through those and what did you learn from that experience?
I worked at Apple in the interval where Steve was gone. John Svelli, that kind of period. So system seven, system eight, Power Macintosh, like that whole era. And we were doing a lot, you know, we shipped a bunch of great hardware. We transitioned the company from Motorola 68,000 CPUs to the PowerPC architecture, but
Particularly in that transition, we really struggled to ship consumer software features. I mentioned, you know, I wrote 300 folders and some other consumer features like in my first six months at Apple and they shipped four years later, actually after I left the company, I was a little surprised they were still in the software repository even, candidly. But I'll tell you that one of the things like culturally about Apple in that moment was, at least I felt like,
A person was really rewarded if they could make a broad contribution across functions. So if you were a talented software engineer, but also a thoughtful product designer, and maybe also had interesting input on product marketing,
that you could build a really great reputation inside the company by playing all of those positions a little bit day-to-day. And so when I left Apple after four years, I looked back at my time. I didn't ship as much software as I had hoped. And I felt like a little bit like a professional gadfly. I was like, you know, six miles wide and like a centimeter deep. And I went to the work for this company called Berkeley Systems.
They, in addition to, you know, don't know, Jack, they may be flying toaster screen saver if you remember. Oh, my God. Remember the 90s. I could you forget that. And when I met them, they were kicking off this game development for this, this trivia game. And we're looking for someone to lead the technical team.
And so I joined as technical director for the United Act franchise, managed a team of engineers, and it was a completely different culture than when I was used to at Apple. It was certainly the case that I was welcome to weigh in on
the game design or the marketing or some other aspect of the deliverables. But my job was to build the software on time with high quality period. And if I did those things, I'd be rewarded. And if I didn't, I would not be successful. And no amount of insightful feedback on the gameplay or the packaging or whatever else I might want to do.
what's going to benefit me and my career at all. And it was such a blessing to be forced to go deep on something, because I spent a lot of time developing chops as an engineering manager, but I also wrote a ton of software. And that's really honestly when I became a software engineer. My college education was insufficient to get me there, and the amount of software I wrote at Apple was insufficient to get me there.
But I came out of my Berkeley systems. You don't know Jack experience like feeling like I can really hold my own technically in a way that just wouldn't have happened. And so. I do think that there's something to be said for a culture where there are swim lanes and people are encouraged to be like really really exceptional in their lane and.
So I feel really lucky that I stumbled into Jack when I did. And it was also, I mean, it was the first thing that I worked on that had just like,
huge cultural awareness for a couple of years. I mean, it's crazy. They're still making sequels. It has been nearly 30 years, and there are versions of you down to Jack that are in all of the stores, in the PlayStation store, in the Xbox store, in the iOS store. You can play new versions of you down to Jack to this day. It's crazy.
Did not know that I see the website now, and it's a little different, but basically the same.
So I'd say my lesson for, you know, my lesson for me to honor Jack was definitely like it really does pay to get good at something and not just be a generalist. And then, I mean, you know, Pandora, it was the next thing that happened after you honor Jack with pets.com and then after pets.com there was nuclear winter in the industry and I worked in enterprise software for a while. And after nuclear winter,
I had this idea that I was going to build a destination for music discovery on the web. And I've been doing enterprise software. The consumer intranet was non-existent for those years, early aughts. But around 2004, things started to thaw a little bit. And you started to hear the first signs of the companies that came to call web chutato, like Flickr.
would have been one of the early examples. And one of the enterprise software things I did was a personalization recommendation engine that used a vector space. It's like a lot of the things that we're talking about now in AI, albeit 20 years ago. And so I knew something about recommendation systems in the enterprise space.
I was super passionate about music. I'm not a musician, but I was that kid in college who would corner you and be like, oh, if you like this band, I've got to play this for you. And, you know, stereo until you would like beg to leave. And so I had this idea that like, maybe I can use the internet to do that at scale, not with just one person, but with, you know, hundreds of thousands of people or millions of people, maybe introduce them to music that they would love, but otherwise would miss out on.
And I promise that I was going to tell stories about luck in my career. There's been a gazillion of them, but one really dramatic instance of that is I
I was sort of biting my time to exit this enterprise software company. I was VP of engineering, a whole team that reported to me, I felt a lot of responsibility to exit in a responsible way. But I was really excited about this digital music company that I was going to start. But I wasn't telling anyone at all because I didn't want to get back to the team. So I flew down to Los Angeles to go out to Coachella in the spring of 2004.
and completely randomly physically bumped into a guy that I had gone to high school with on the poet's field.
and hadn't seen him in a decade. And the thing that we had in common in high school was we loved music. And so I tell them the story of the way, I'm going to start this company to do personalized visual music on the internet. And he said, there's this woman I work with who just left our company to move to Oakland to work for this little company called Savage Beast that are also doing something in music recommendation. Do you want to talk to them? And I should sure why not.
So I got introduced to Tim Westergren. I was the founder of Savage B, Savage B used like a seven or eight full-time employees at that point. They made a music recommendation engine that they licensed to other companies to put in consumer products. So Savage B's customers were best by who put it in kiosks and AOL, who used it in the AOL music.
website, and they were looking for a VP of engineering. I got the offer, thought about it a little bit. I declined because it was this B2B2C thing, and I really wanted to do something and get to where I had an idea about the app. A month later, they called again and said, you know, we keep talking to people who really think that you're the person. Interestingly, one of the many reasons they thought that I was the person is they were really impressed by the fact that they had run engineering at pet.com.
So I mean, it's one of those things where like these things to pay dividends even when they're a disaster. And honestly, in like what I would really say was like almost like a lapse in judgment, I said yes, even though it wasn't the product that I wanted to build.
I won't bore you with all of the details, but 90 days later, after some typical early stage founder drama stuff, the founding head of technology and product had resigned, completely unrelated to my arrival. The company had a new CEO, Joe Kennedy, and Joe had this idea for what he called a one-click personal radio.
Joe is a product marketer and just the best CEO and whole. We're always spent 10 years together building Pandora and.
He sort of gave me the keys and just said, as long as it fits the brief, one click personal radio, it's all yours. And I had to build the team and the culture in collaboration with him and Tim, the founder, over the course of the next 10 years. And it's just every good thing. So I mean, there's just a million billion lessons from Pandora. I mean, everything I am as a product leader and an engineering leader comes from things that happen at Pandora.
But maybe the thing that I think of first is I think we met our early audience in an incredibly genuine way. For example, when we launched the support at Pandora.com was an alias for all at Pandora.com. So if you send a customer service request to Pandora, every single person in the company
received it. And because we had no, we made a decision to have no customer support team in the first year, the expectation was that whoever sees the request first should respond to it. And so, you know, you would write to us and you would get the founder or you'd get me or you'd get the engineer who wrote the feature, you'd get the CEO and there were no
There are no macros to, like, respond to a commonly asked question. There was no read the FAQ. And there were no rules about what you could and couldn't say if the person's like, I think this feature is stupid and broken. We would encourage people to say, like, you know what, I think you're right. And I'd like really struggling to get our stupid head of product to agree with me. I would just, you know,
I'm going to CC Tom and maybe we can convince him that, you know, this was a bad decision. And we did all of that because we thought one of our like superpowers as a young company was that we could just like engage with our audience like real human beings, not like as a shiny brand that was trying to, you know,
you know, be something that we could just never be. Like this is, this period is where the iPod and iTunes are like the peak of their powers. And so, you know, there was no way we could sort of out Apple, Apple on the brand front. And so we were just ourselves, and I think it really, really was a catalyst for the word of mouth that developed around Pandora, and like we never spent any money on paid user acquisition, like literally no dollars the entire time I was there.
because people love the product and they told their friends about it and that's how it grew. I saw a stat that you grew Pandora from 80 million users from 10 employees to 3000 employees from zero, basically it's a multi-billion dollar company. So we did those things. Not bad. We did. We also, I mean, I think my product stewardship in some ways set the scene for Spotify to walk through the digital streaming door and show us the exit.
So Pandora is, I mean, again, such a privilege to be able to work on something that touched and continues to touch tens of millions of people's lives every month. But it's bittersweet from the standpoint that I think we had an opportunity that in some ways we misplayed.
My mom is still a huge fan of Pandora. It uses it every day for whatever to me. I mean, it's still going. And then there's like the numbers are still tens of millions of people in the US listen every month. So it's a thing. But yeah, I mean, it's a little sad that it didn't it didn't have the quite the staying power that some of these other things have come along since half.
Just on that topic, do you think there's something that you could have done, someone could have done? Do you think there was an opportunity to become Spotify, or is it the business model and the math formula was set up in such a way that it was nearly impossible?
One of the things that was tough for Pandora was that when we started it, digital music was like a category that no investor wanted to touch. It was lawsuits, there was no money to be made, there were relationships with the labels that were completely impossible to nurture, and there have been no big outcomes. I think the biggest exit in digital music
when we got going was a Yahoo had bought music match for like $400 million. And so that was seen as like kind of the ceiling on the opportunity. And you know, along the way, we found investors who believed in our vision and invested, you know, ultimately hundreds and millions of dollars in the company over its pre-public years.
But there was never an investor enthusiasm for the company in the category that was anything like the investor enthusiasm that a company like Spotify enjoyed just six, seven years later. Snap enjoyed for its pre-public tenure. And I think part of it was different for Spotify is that the comps were not music match at 400 million.
Pandora at $8 billion, but even above that, they were Netflix at $100 billion. Investors just had this new optimism about what you could do in subscription and in streaming.
Spotify really played that to their advantage in a way that we couldn't because we had gone public and the public market investors were still trying to figure us out. So we didn't have access to capital. It was very hard for us to take the same kind of risks that Spotify took.
But then I think we just completely misjudged one really important thing, which is that we were really inspired by disrupting terrestrial radio, terrestrial radio is like the predominant form of music consumption in the country. You know, people spend, I can't remember the exact stats, but it's like, you know, by minutes consumed, it's something like 10 times more music minutes a month on the on radio in the aughts and
early 10s then on own music and the advertising supported sort of radio market was
$30 billion category and recording music with $8 billion. And so we had this idea that we're going to reinvent radio and Spotify and RDO and Apple Music and like the 14 other, um, Rhapsody, which was Spotify before Spotify, they were all going to chase this smaller, re-owned recorded music opportunity and that
you know, we could be left relatively alone over here going after the less sexy but actually bigger market. And I think we just got it wrong. It should have been obvious that inevitably all of your music in any format was gonna be delivered, you know, as a stream from the cloud,
and that the record labels in particular, they were going to set the terms on what the structure was and the structure that they preferred was the Spotify structure.
We operated under a different licensing regime that they hated. That was a statutory license that we got from the government. And it was exceptional, it would have been exceptionally risky for us to come out from under the statutory license and do direct deals with the labels. But it was a requirement to play in the world that they imagined as the future. And we should have imagined as the future too. And eventually the company got around to it and that it was too late.
It's interesting that so much of this was rooted in that original vision that you shared of Pandora, the radio, smart radio in your pocket. Yeah, one thing for radio. Yeah. One thing for radio that's like you just stayed on that track, even though there was this other track. But I think it's important to point out, you said it was like seven years later. And I feel like there's this interesting trend with the companies you worked at, pets.com.
and Pandora that is too early. You just come too early at these ideas. And I feel like that tells me Quibi might still happen. There's a Quibi coming seven years from now. You know, it's really, really funny about that. Just today, there's a headline.
about a Hollywood-produced show that's launching on Instagram Reels and TikTok that was shot vertical. And the headline is literally something like, is TikTok the new TV? And it's pretty funny that literally that's what Jeffrey and Meg called it when they were incubating the idea.
I mean, I think it's pretty clear that purpose-built video for mobile looks a lot like TikTok, and I don't want to take anything away from all of the innovation in that space that they and the other players are driving, that Quibi didn't capture in its initial product definition. But, I mean, you know, obviously we started our phones consuming video of all kinds, you know, all day, every day, so there's definitely something there.
The PDF that I mentioned that I got from the recruiter, the first page, again, says, you have a TV in your pocket. So it's exactly what they're pitching. That's amazing. All right. I think what I've learned, I need to bet all my money on the Snoopy B clone, because the timing is timing might be right.
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Let's talk about Snap briefly and then I want to have a couple more questions.
I mean, Joe was like all things. He was an engineer by education and a great marketer and a great finance person, and just such a utility player at a very, very high level across every discipline. But he was also really, really good at letting his team do their jobs. He really let me run product and engineering.
You know, not only did I have tremendous latitude to make good and bad decisions about product, I also got really got a seat at the table to like help lead the company so rewarding, so gratifying, best professional experience that one could have. So I leap into or after a decade, I take like a year,
and trying to figure out what I'm going to do next. But after about a year I got introduced to Evan. And it's kind of a funny story. A mutual friend sent this introduction over and then immediately responded and said, why don't you come down to Los Angeles and have a coffee with me?
So I fly down. It's not clear if it's a job interview or like what it is really. I mean, I was just like lightly exploring things that were out there and was a big fan of what he was doing with Snapchat. So I spent like 45 minutes with him. And then I spent 45 minutes with the head of engineering and another 45 minutes like that had a legal. And then they tossed me into a conference room with like a dozen product designers.
all their mid to late 20s, many of which are that gone to school at Stanford with Evan. I would come to learn like all really, really, really impressive, super, super talented people, but like, you know, it was just like 10 of us sitting right at a conference table. And it wasn't like clear that they knew why they were talking to me, but we had kind of a, you know, hour long free ranging conversation. And, uh,
So I left and I thought it was like, it was like a totally fascinating morning, but I wasn't sure what had happened really. I was like, well, with these interviews, like it all seemed very ad hoc. Is there a job opening? It was a little odd. And I...
I went to lunch at Anabic Kinney and got a text from Evan's admin saying, can you come back to the office if you've gotten on your plane? I was just ordering lunch. I'll just come back right away. So I go back. Now it's like one o'clock in the afternoon. This entire thing started nine o'clock in the morning.
I sit down at conference room, Evan comes in with a Manila envelope and says, we loved you, we'd like for you to be our VP of product and like handed me a written offer. Like all the terms, like the stock compensation, the whole thing.
I'm gobsmacked. I'm flattered. This is really playing to my ego. I can't believe that this company that feels like maybe the most interesting thing that's happening in consumer tech that notoriously brilliant and mercurial founder has taken enough of a shine to me that he wants to give at least some of the keys to the product kingdom over after such a short courtship.
So I leave and when some of that buzz wears off, I start to wonder if there's like some red flags or maybe. So I tell Evan, listen, I like to come back and meet more of the leadership team. So more time with you, go a little deeper on what this means. And so we send our courtship by another week or so. And I, you know, super impressed by the rest of the leadership team and the product thinkers and
stuff for desires and things that I was gonna get to work with on a daily basis.
So I take the job, full knowing, that it's going to be wildly different than Pandora. We had all of this latitude to do whatever I might want to do. And in the context of Snapchat, at best, I was going to be Evan's right hand, a person that principally executed his vision. And that's certainly what it was. Evan and I ended up having a really great collaboration
But it was certainly most days I was executing on his vision, both at a high level and very much in the details. And Evans truly brilliant. And he's also actually a really nice guy. I think in some ways he gets a bad rap. He has very high standards, but he's a very kind person in my experiences with him.
But it was a super exhausting job and not as soul satisfying as I wanted it to be. And after a couple of years, I, like I said, I thought maybe I just wanted to like make croissants or something. But one, one really, really big important lesson that I learned at SNAP is about risk taking. And like when you have the,
The financial support and the foundational relationship with your investors that Evan has, it really allowed him to take these really big swings. You know, acquire technology that he thought was game-changing, build features speculatively that maybe would be pruned in any other product or map planning process because the odds of them having an outside impact were modest.
And it just allowed him time after time to make bets that paid off. And we forget about the ones that don't work when there are so many home runs in those years. And we didn't have environmentally, we weren't set up for that at Pandora. But I think in some ways, I wasn't temperamentally inclined to those kinds of big swings. And I think I'm a, I take bigger risks and encourage bigger swings now because of things I learned from Evan and Snap.
That is an awesome story. It resonates a lot with what Brian shared about how he thinks about product now, which is kind of.
telling people kind of what to build versus very bottom up, tell us ideas you have. That impact the way you run, we're going to talk a bit about you as CEO now, but I guess you have a place to try to be of CEO as here's what we're building. As a product oriented CEO, like how much you should kind of lean into the details versus
set direction and create an environment where great people can do great work. I suspect there's not one answer that applies to every company stage. When I was at Apple, one of the reasons that we struggled to ship things is that
Apple did a great job of assembling incredibly, incredibly smart and talented people. Just like everyone around me at that early stage in my career was so, so inspiring. But one of the side effects of that is we would get in a room and we would turn over some problem or opportunity and we would talk ourselves out of every good solution because it wasn't perfect.
I used to joke that the only place in the world where a vote of a thousand to one was a tie, because that one person would be so thoughtful in their critique that the other thousand people would be like, that's right, that's right. And even though there's been this huge consensus of what the radiator was, we were going to talk ourselves out of making decisions. That one wasn't Steve Jobs necessarily could be somebody else. Who wasn't there?
So I think what broke Apple out of that mode was Steve came back and they didn't vote anymore.
Right. You know, Steve was just making the call. And so I have some sympathy for Brian and Evan who have these big, you know, thousands of people working for them. And as they delegate, they, they grow frustrated that there's not progress at the pace that they're looking for and that there's indecision and the people on the team's report that there's just like churn and no progress.
There's victims in politics and all the rest, and that is the CEO is a brilliant product-oriented CEO. They are uniquely situated to come in and cut through all of that garbage and get the trains running on time again.
Having said all of that, I also think that it can be a mistake to be that kind of leader in a smaller org, because part of the opportunity, the small org is to assemble a group of people that are incredibly talented that believe in your mission and who you can easily influence with a much lighter touch and set them up to build a culture and an organization that can execute. I see
I see my job as CEO is to try to surf that edge of like, I'm really in the detail so I deeply understand the business and the product decisions that we're making and the processes that we're using to run the business, but not overplay my hand with respect to dictating outcomes.
The one we always have as CEO is no matter how much you tell the team that when I swing by their virtual desk and say, you know, I've been thinking about this little detail. I thought important right now, but like, what do you think that the, you know, it's like nine out of 10 times that person is going to go and start working on that thing. And so you do have to be just really careful about the way you engage in some of those details, I think.
There's a really good episode I had with Lane Shackleton from Coda, and he shared this framework called Flashtags that they use at Coda. And I think it comes from HubSpot. You tell people here's the, what this opinion is, is it an FYI? Is it a suggestion? Is it a do this? There's like four of them and one's like, I will die on this hill. You need to do this. I try to do a lot of that.
I wish I could say that, in my experience, that pays off a lot of time, even as I say, very clearly, just one person's opinion, focus on what I need. Don't change your priorities to go work on this. It has more of an outsized impact on people's behavior than I do. Easier said than done.
Coming back to your journey, we've talked through the story up until getting to Quibi. But two years ago, you went in a whole new direction, and you're now the CEO of a company called Zero. What is it like to move from just being a product leader and engineer leader at a company to being the CEO for the first time? Why did you use Zero as that role? And what have you learned as CEO that you wish you knew as a product leader and engineer leader at a company that listeners might find useful?
It's been a really, really incredible couple of years. You know, in the aftermath of Quibi, I spent a lot of time sort of as me, I'll do sort of, you know, soul searching about what I learned and what I might want to do next. And, you know, as I thought about it, I realized that I really wanted to move on to something where I could have like a direct impact on the culture and values of the company that I was involved in. I really, you know, got that opportunity at Pandora in a big way. And, you know, I had spent the
five years of Snapchat and could be working for Evan and Meg and Jeffrey who are all incredible business leaders but have their own very specific sort of style and approach and that leaves a mark on the culture that's unique to the founder. And then as we discuss, I'm always really interested in
and building things that are near and dear to me. And I was particularly thinking about what can I do that could have a really positive impact on the world in my next chapter. I've been off a lot of media stuff through the years, video games and streaming services and so forth. And it seemed like maybe there was something that was a little bit more weight to it that I could spend my time on.
And so, you know, my first thought was I would start something. So I had a company idea. I was kind of quietly workshopping for some months and completely independent from all of that.
It's eight months into the pandemic. And my own personal health was at an all-time low. I was 50 or 60 pounds overweight. My cholesterol was in the red zone. I mean, I was out of breath climbing stairs, which is something that I had never encountered in my life before. I'm a bit of a yo-yo dieter, and I'm always kind of critical of looking in the mirror. But I was never ever really worried about
health my longevity and suddenly I was and so my solution to that was to like go really deep on metabolic health like just like thousands of hours of podcasts and videos and you know glucose monitoring patches and aura rings and digital fitness gear and just to try to understand you know the things that impact health and longevity and and
You know, as much as I would like to report that when I learned is that there's some like magic pill that you can take, maybe some like ossleable raphemitis or something, the truth is that to live a longer and healthier life, you really have to attack what I would call metabolic disease, which manifests in overweight, obesity and prediabetes and diabetes and high cholesterol and all of these things that impact your large-term health. And so I found zero in this path
and was using it to help in my own sort of health journey. And Mike Maser founded the company four and a half years ago, and he and I were talking in this interval about my own experience, the product I was just kind of giving him products, he backed and so forth. And he was telling me a little bit about his own entrepreneurial journey. And somewhere in the conversation, Mike said, you know,
My intention is to step up into the executive chair role and to find a CEO for the company. So again, like in my story, just over and over and over, this incredibly fortuitous thing happened. You know, I just sort of knew immediately that it sort of ticked all the boxes. You know, here's a chance to
you know, lead something that already had some momentum to impact the culture and values in a really direct way. And was like really, really close to my own personal journey. And so, you know, we've got a great little company and 27 people. We've got more than a million users on the platform every month than over 100,000 of them pay us with tens of millions of dollars of revenue through the years. And you had double digit growth even coming out of the pandemic when lots of health and fitness companies kind of saw retreats
And most importantly, it actually works. 75% of the people who use the platform lose weight. People lose on average 5% to 10% of their body weight in the first 60 days. And because of the success that people have, we grow just completely organically. We have no paid user acquisition at all. It's really a word of mouth business. But that's not to say that it's not challenging. All startups are challenging.
What we've really focused on for the last couple of years is we've been really focused on unit economics, like really trying to understand how much value can we derive and deliver for every person who downloads and installs the app. How do we convert them through all of the funnels efficiently and get them engaged with the product and get them to retain and sort of drive that up in a really systematic way.
You know, I'm, you look at my whole career, I'm definitely a person who started off stinking software development. It was mostly in correct form. You know, you find, you know, brilliant visionaries who have a deep understanding of human behavior and they craft solutions for problems that other people don't see and they make them delightful and they get all the little details right. And, you know, when you found product market fit for the art, then,
You sort of optimize them through a really sort of quantitative sort of take. And so I'm definitely a person that sees both sides of that sort of left brain and right brain equation. That's important in software. But here's the thing that's really
My eyes have really opened to in the last two years. Well, companies are definitely the software that they make and the products that they deliver and that there is an art and science to that. As I described, there is also, if you step back, there is an equation that describes the business. It talks about like how you turn investment into returns. And I suppose I had come up with finance and then a business major that maybe that's the way that I would
conceived of companies to begin with. Maybe it's a little embarrassing. I had to be 53 years old before I, like, the scales fell through my eyes and I was like, oh, like companies are equations.
And so, you know, when we first started talking about lifetime value and customer acquisition costs and getting those two things balanced and just sort of thinking about the unit economics of the business, my natural instinct was to go immediately to sort of the leaf nodes of the equation like, oh, what percentage of people do we convert from install to registered and from registered to trial? And these like very sort of way down at the bottom of all the funnels and to like ask the product team, like, let's try to optimize these.
And in the process, though, of trying to understand where we could take the business as we optimize those various dimensions and trying to understand, too, which of the dimensions had the most leverage, I started building these ever more sophisticated models that describe the whole business.
I mean, it started to get to where a lot of hats and definitely a hat that I'm wearing that I didn't anticipate at all. And I am the full-time FP&A guy for zero. And so I built this spreadsheet that aggregates data from all of our business intelligence tools and raw data from our subscription transactions and looks at all of our historical results and all of our expenses and spend and then could use that to
predict future scenarios by sort of manipulating all of these variables. And it's just not at all the way I ever thought about products before. And I know that you've got lots of listeners who are like, this guy's an idiot. This is a fundamental way to contemplate product work. But if there's anybody out there like me who sort of thought of it as arc first and then sort of optimization in the details, it is really, really powerful.
to spend the time to create the model that describes the whole thing so you can identify what are the high leverage points to focus on. So we've been doing a lot of that at the company in the last two years and it's really starting to deliver incredible results. You know, like everything in life, you just sign up for things so you can learn and that's the big one for me in the last year.
I really love that takeaway of as a CEO coming back to share, here's what you should be thinking about, that the CEO is probably thinking about as a product leader, you may not be, of trying to actually spend the time to think about the business model and understand it deeply because your founders are thinking about all the time. And so if you're not, you're missing out on like, here's a way to influence them, here's a way to. It's so funny too, because it's a thing, I suddenly understand something that mystified me through my entire career, which was,
I go to board meetings and the investors would ask these probing questions, but they were really never about the product and what the product did and what the product roadmap was and what the features were. It all seemed to operate at this level that was almost completely independent of the details of what is the solution you put into the world, which is the product.
you know, oriented thinker was just completely baffling to me. And I like, I now realize that they were, they were tilling the soil that I'm talking about. They were tillingly what it, it doesn't really matter what the screens are and what the features are. And like, you know, that means it really matters. But like if there's another higher order way to look at a company, which is really about the optimization of this equation. And I think particularly if you sit on 25 boards,
It's probably a much more efficient way to evaluate how your companies are doing and where to spend your time and how to help by thinking about them abstracted up with that layer. So I will never stop thinking about software development as being in our form and I will never stop enjoying the days when I get to sort of lean in on the details, but it's been pretty eye-opening.
The other thing that stands out here, one is, I think this is especially true for consumer subscription apps, which I've done some research on, and basically they never work. There's Duolingo, there's zero, which I didn't know how much scale you guys reached. My math here real quick, so you have a million users, 100,000 paying users. You charge like 10 bucks a month. I know there's a discount for an annual plan, but basically you're making somewhere a million dollars a month.
which you don't have to confirm or deny it, but that's the math I just did. And that's crazy. So congrats. That's a rare, successful consumer subscription app. It never happens. And like I said, every time every startup is hard and I never stopped being surprised at the new hard things that pop up every day, but we're on a really great run. We've had a tremendous year and I'm just so, so proud of the team lead assembled. They're, they're incredible to the last.
Part of the reason you're so successful is exactly what you said. There's a huge focus on LTV, CAC, the math formula because for these sorts of businesses, that's the crux of it is can you acquire people for less money than you need to spend. One thing that's really fortunate for zero is my major who founded the company and I have both been sort of around the block long enough and enough times that we remember 2008, we remember 2000,
And so in these moments, like kind of in the pandemic, you know, there were companies in our category that were raising hundreds of billions of dollars with the intention of sort of throwing it at pay user acquisition. And we made a conscious decision to
to optimize the value of the organic traffic that we were getting into drive our growth through LTV expansion rather than top of file expansion, which was candidly not in fashion in 2021, 2022. Turns out it's much more in fashion these days, as companies are called upon to be much more capital efficient than they were during the pandemic era.
I guess I feel somewhat fortunate that my natural inclination as an entrepreneur is more in sync with the expectations of the market than it was for a while. You've probably had the longest career arc of anyone I've had on this podcast.
You've worked at all of these different companies in a lot of different phases. You're still at it. And I'm curious what you've learned about how to maintain your mental health and avoid burnout essentially through this journey. You mentioned you take some time off. Is there anything else you found or is that is that a trick of just how to not burn out? Do you know this, this, this Japanese concept called ikigai? Yeah, but share it. Share for folks that may not be familiar.
So the idea is it's a Venn diagram, and there are four spheres. There's a sphere that's labeled what you love.
There's a sphere labeled what you're good at. There's a sphere labeled what the world needs, and there's a sphere called what you can be paid for. And where they all intersect is this Japanese idea that they could guy. It's like the intersection of what you're good at, what you love, what the world needs, and what you can be paid for. If you find that, it's a guy.
Interestingly, your listeners should go and find this because there are interesting ways to label the other intersections, the intersections that were they all for don't come together and
And what's really interesting is that the ones that are three but not four, I think because they are, they're the ones that are like close but not quite to this really satisfying thing. And so it's like when you find those, it's really easy to choose a job or to choose a path where you have three but not four, which is a really great recipe feeling like there's something just out of your reach that's really important.
Anyway, it's a great framework to think about your life and your career. So to start, I'm incredibly lucky that it's all a good guy for me. What I'm good at, what I love, what the world needs, what I can pay for.
They're just, they've always overlapped. And a big part of it is just like, what I love is this world. Like I love software, I love building software, I love writing software, I love using software. Like people are like, you know,
What are your hobbies? And I'm like, I don't think I have any hobbies. And I think about like, well, what kinds of things do I do on the weekend for fun? And it's like, you know, I'm like teaching myself after effects or something, which I will immediately forget. But like, you know, I just.
like it's just sort of fun to go really deep on some piece of interesting software. So I'm very lucky. And so that, I think that has been super sustaining for me, you know, like one of the reasons I've been able to do it as long as I have without really burning out is that just like, it's what I do it. And some reasons why I come back to it, like it's easy to say I'm going to become a pastry chef, but like left to my own devices.
Like, I use software. I make software. It's my hobby. It's my passion. It's all the things. But a couple of thoughts about how one engages with their work. One thing is I'm really not like a hashtag hustling kind of leader.
There was a woman that I worked with on the finder just out of college that left a really big mark on me. My own style of work, then, I think I mentioned that my memory of flashing, like, linking the folder animation was like a 2 a.m. kind of thing. I mean, I was 23 years old. I woke up at 11 o'clock in the morning. I went to the office.
I screwed around and played, you know, video games and the Apple Arcade and went to a couple of meetings and had lunch and stood at the whiteboard and pontificated about some nonsense. And then about four o'clock every day, I would start writing software and I would write software until two or three in the morning. And then I would go out to dinner with the people from the team in the middle of it and whatever. And so it kind of looked like I spent 14 hours a day
six or seven days a week at Apple. And it was, I was really, I was celebrated for this with lots of nights where I was like, we're clear through the night and my boss would come in the next morning and you're like, are you still here? And I'm like, I'm still here. Look at the school thing I did. And I got a lot of attention for that. And then there was this woman on the team who showed up every single morning at 830, sat at her desk, wrote a ton of great software and every night packed her stuff up and left.
And she contributed more than I ever did. And I don't think she got the same kind of recognition that I got because of the way she did the work. And when we were building the team in culture at Pandora, I thought about her a lot and really made a point of saying that I just wasn't interested in like performative contribution, that it's the work that matters and
What I want to celebrate is if you can show up and do it and go home and have other things in your life. Because I think that's a recipe for being able to do it on a sustained basis rather than kind of burning yourself out. I think there's some nuance in this. I think 22 year old me.
was always going to want to work through the night. And so I think creating space that that's okay too is important. And I think maybe in some ways at Pandora, like it was almost like that wasn't okay. It was like you should be taking more breaks. Why are you doing going this hard? But I do try to create environments where people have like a reasonable balance between a regular life.
and their technology life, or room for that if they choose it. And I do think that that helps through the years to help me keep at it. But I still work a lot of nights and weekends because I love it. It's my, you know, it's what I do. Here's the other thing. I'm very, very lucky with the Pandora experience at this sort of, you know, outsized, probably inappropriate financial reward for being a part of it and gave me options that I never imagined that I would have.
And so I, after 10 years, I left and I didn't know what I would do, but I thought maybe, I mean, I really need, I did really need a break. It was a really hard job. And that was definitely a moment where I needed some time to recover. But I think if you asked me on that first day, I would say like, I don't know why these people like find success and then like start another company right away. Like, why? Like, you know, so many things you could do in a while, why would you start another company? It's so hard.
And I was particularly in love with the idea that I would like, I had access to experience. I didn't really care about things, I don't wanna fancy watch or whatever, a car, but I wanted to see the world, kind of. And so I thought, I'm gonna just go and I'm gonna live in London for three months. If I'm actually in Cisco for a month, I'm gonna live in Mexico City for three months, and I'm gonna just have this life where I'm soaking up experiences.
And after doing that for six months, the thing that came to realize is that what I care about way more than experiences is relationships. And if you're the person who is constantly on a plane, seeking out some new experience, it's really hard to form and maintain intimate, satisfying relationships. So I went back to San Francisco. I can't be all over the world if I want to be engaged with friends and minded people.
And you know what people do on Monday morning? They go to work. And so like if you want to be engaged with humanity, like where they are on Monday morning is like at work.
And so more than I had the itch to build things, which I do very much have, I had the itch to collaborate, to like be in the game with other people. So that was what took me to Snapchat, took me out of like chasing experiences and took me back to building again. And then if you've already described like, you know, I had a point I thought, well, I care about like this.
this collaboration, but maybe it doesn't need to be software that I'm creating in the world and could be like gave me a chance to sort of fall back in love with that process again. And here we are, more software.
plus being on board of a hardware company. What you just shared reminds me of Mark Manson's book, The Subtle Art of Not Giving a Fuck, where his... Have you read this book? I've not. Okay, it's like sold like a bazillion copies. And the core of it is that we get joy out of solving problems, and we think we'll be happy when we have freedom to do nothing, but it turns out freedom is only helpful to help us discover the problems we just want to keep solving.
Yeah, totally. I think that's exactly right. Yeah. Sounds like that's the experience you went on.
Last question. I'm trying to, this new segment, I'm going to call a contrarian corner. And the question is, is there something that you have a contrarian opinion about, something that you believe that most other people don't? There's segments in our industry that believes this like, uh, very intensely, which is like, there's this belief that everybody needs to be a founder. And I think in some ways, our industry would be much better off if there were fewer founders. I think in some ways, the,
It's an entire category of smart, creative, hardworking, talented, borderline visionary people who can raise that $2 million seed and go off and build some stupid company that's never gonna go anywhere. That would be so much better off finding a team that needs their skill set and working on a problem that has,
that doesn't like, as I described, the mathematical formula that's going to win and has the market opportunity that's like the rate size that like, you know, has the 10x thinking that can really, and, you know, I'm a little biased here because I'm, well, I am, let's see, you over the first time now, I've never been a founder and I've been lucky enough to find a bunch of young teams that could benefit from my
skills and enthusiasms and sometimes to some success and sometimes to some embarrassment but always really really interesting.
Yeah, if you're out there and you think that the only possible way you can be successful in this industry, on any metric, whatever metric you care about, you want the acclaim of your peers, you want financial reward, you want any of the things that people aspire to, you want an outside impact on culture, whatever the thing is against you out of bed every morning, you can achieve that in collaboration with
with others, you don't have to be the person that that raises the sea ground. I 100% agree with that. I'm always telling people don't start a company. It's super painful. Very rarely works out. It's like so hard. I don't know what's harder being a product manager or being a founder, probably being a founder. They're both very hard. Yeah, it is quite hard too. Yeah.
Yeah, I mean, just to be perfectly clear, there's something really special about founders at both Pandora and now at zero, the actual founders have from time to time said, well, you're like a founder and I'm like, I'm nothing like a founder. You took all the risk. And when I showed up, there was a team and there was momentum and there was money in the bank. I appreciate your desire to say complementary things, but you're like a founder is not one that I'll take.
With that, we've reached our very exciting lightning round. Are you ready? I am ready. What are two or three books that you've recommended most to other people? I really love Elad Gil's High Growth Handbook. It's organized into chapters about sort of foundational company building, building leadership team, building a board, and
In addition to the thoughtful synthesis on that topic from a lad, there's also like an interview of someone that he does relevant to that section on each of the chapters. Really, really great read and super actionable if you're a leader in a young company.
I mean, a completely different end of the spectrum. I love big complicated science fiction. And I mean, there's like a lot of garbage science fiction out there to be sure, but when you find something special, it's like, it's the best. So probably through the years in that category, there's a book called Hyperion by Dan Simmons. That's, it's just like a total classic. Everybody should read it.
I read that. I think I read the first couple in the first one. Yeah. There is a sequel that's exceptional as well, and it's probably worth warning your readers that Hyperion is quite long and has an absolute cliffhanger. I think they're making a show out of it, which is going to be wild. I don't know how they do a show around that book.
I thought you were going to say this other book, A Fire Upon the Deep. Have you heard of this book? Oh, that's so good, too. That's also very complicated, but incredible. Yeah. I had completely forgotten about that. That's a very special book. There's a couple in that series, too. Yeah. I think I only read the first one. Also, three-body problem is the other one. Yeah. Always think about it. It's come up a couple of times on this podcast.
Let's move on to the next question. Do you have a favorite recent movie or a TV show? I consume a lot of video content, both like, you know, stuff that I'm very proud to talk about and stuff that I'm less proud to talk about. But I really liked the new Damon Lindelof show that's on Peacock called Mrs. Davis.
So Lindelof, of course, from Lost and the new Watchmen on HBO. And Mrs. Davis is about an AI that you wear in your ear, like the her AI and a nun that is hell-bent on the AI's destruction. And it reads like an early Cohen Brothers movie.
It's super darkly funny and really, really thoughtful and unlips too much streaming. I think it's seven episodes and it is a perfectly encapsulated story that has a beginning, a middle, and an end and doesn't need to ever have another episode. It's amazing. It's worth the, you know, get yourself a peacock subscription for at least a month to watch Mrs. Davis. Favorite interview question you like to ask candidates that you're interviewing? They're two things about interviews. The first is I always encourage people
When they're thinking about their interview questions, to take any question that they're tempted to pull from their own current experience with the goal of trying to, how would this person solve this thing that I'm working through right now? Because it just calls in the other person to speculate, oftentimes, about your own business. I think you know really well that they don't actually know anything about.
It creates this imbalance between the interviewer and the interviewee that feels like out of sync with how I think about the collaborative nature of a great interview. I tell people that almost every interview question should start with, tell me about a time in your career when?
to just to give them permission or to set their expectation that I'm asking them to tell me about something they've actually done that is relevant to the topic that I'm probing. So that's just a structural thing that I try to do. And then usually towards the end of the interview, I ask almost everybody, imagine you have a really great day at work.
Tell me about what, like, what was it that you did on that day? Because I'm trying to figure out is kind of like left to their own devices. What do they go to naturally because it rewards them?
Because I think it's really important to find the highest best use of everyone you hire. And sometimes you can get a little bit to the bottom of like, what's the highest best use if you understand the things where there's a natural reward mechanism because it's like, well, I had this great day. I'm going to do more of that tomorrow. What was the thing? And it's just a pretty illuminating. Is there a favorite product you recently discovered that you really love? I had bought every pair of headphones on the planet.
in part because Apple's headphones do not stay in my ears. They just like, I've sneezed one across the room. I've lost one down a drain pipe. They just, they don't stay. They never, none of them though. The wired ones, the not-wired ones, the in-ear ones that they're just, and it's left me feeling honestly like I am some kind of anatomical freak. Like I will look at other people wearing them and I'm like, what is going on with their ear that it's just staying there? Perfect. It seems inconceivable to me.
Nonetheless, I have a pair of AirPods Pros that I want to love and kind of put up with the fact that I'm going to drop them, lose them, sneeze them across the room. But recently, I came across this product.
from a company called EarTune that are these kind of their replacement tips and they just have like the littlest bit of like compression foam on them. So they still, they don't make the AirPods so big that they won't fit in the recharging case or anything and they work.
Miraculously, they stay in my ear, and Apple has this feature called, like, size fit or something. Go on settings, find your AirPods, scroll the way down in the settings, and you can run this test where they play some audio and they tell you how good the seal is.
And that revealed that my right ear is weirder than my left ear, so I actually have to use different tips and either sizes. Suddenly, this sounds like a vaguely disgusting conversation that we're having. Anyway, I'm just really thrilled about my ability to wear apples, earpods, and for all these years. I think we're learning as yard mutants. Your ears are.
different. Cool. We'll link to that product in the show notes. Okay. Do you have a favorite life motto that you often come back to or share with friends, either in work or in life, if I'm useful? I mean, you can't be like a product person without having an eye rolly Charles Eames quote that's at the center of your existence. And for me, the Charles Eames quote is the details are not the details they make the design.
And I just really absolutely believe that the devil is in the details when you're a product designer and be uninterested in nuance at your peril.
Final question, you worked with the creator of the GIF format. How does he pronounce GIF or GIF? Yeah, so before all of this, I worked at a company called CompuServe when I was in high school. CompuServe, I used CompuServe. I didn't know that. That's amazing. There was a guy on the team named Steve Wilhite, who invented graphics interchange format, GIF.
And he was a straight out of central casting 1960s neck beard programmer type. And the first I had ever encountered, and very prickly. And it's crazy, but at the time, Steve would take all comers in the fight that it was pronounced, Jeff.
Now, he's obviously wrong. It's obviously pronounced. It's crazy to me. Now, 35 years later, this is still a topic that pops up on the internet every once in a while. It's somehow like, I cross paths with the guy who created graphics interchange format. And I know his opinion on the topic, even though it's an unpopular one.
Got it. So he likes Jeff, but you agree it's a gift. It's definitely a gift. It's obviously okay. Great. We've decided. Let it be known. Let it be known. Tom, we've talked about successes. We've talked about failures, mental health, general health, all kinds of awesome stories.
Two final questions, work in folks flying online if they want to reach out and maybe ask some other questions that I didn't ask. And how can listeners be useful to you? I'm at tconrad on all the socials from Twitter to threads to Instagram. My DMs are open everywhere. And I really, I would absolutely be delighted to hear from an Adria listeners on any topic that they choose.
And you know, what can you do for me? Well, I would love for folks to download zero and give it a try and send me some feedback about what we're doing right and what we're doing wrong. And we'd love to have our little product be part of your life. Awesome. Tom, thank you so much for being here. Thank you. Bye, everyone.
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
